(10R,11R,15R,16S)-16-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one

• ChemBase ID: 72913
• Molecular Formular: C21H20O8
• Molecular Mass: 400.3787
• Monoisotopic Mass: 400.1158176
• SMILES: c12c(cc3c(c1)[C@H]([C@@H]1[C@@H]([C@@H]3c3cc(c(c(c3)OC)O)OC)C(=O)OC1)O)OCO2
• Canonical SMILES: COc1cc(cc(c1O)OC)[C@H]1[C@H]2C(=O)OC[C@@H]2[C@@H](c2c1cc1OCOc1c2)O
• InChI: InChI=1S/C21H20O8/c1-25-15-3-9(4-16(26-2)20(15)23)17-10-5-13-14(29-8-28-13)6-11(10)19(22)12-7-27-21(24)18(12)17/h3-6,12,17-19,22-23H,7-8H2,1-2H3/t12-,17+,18-,19+/m0/s1
• InChIKey: YVCVYCSAAZQOJI-JHQYFNNDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10R,11R,15R,16S)-16-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one
• IUPAC Traditional name: (10R,11R,15R,16S)-16-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one
• Synonyms: DMEP; 4-Demethylepipodophyllotoxin

Database IDs

• CAS Number: 6559-91-7
• PubChem SID: 162037833
• PubChem CID: 122797

CALCULATED PROPERTIES

• Acid pKa: 9.330433
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 1.4768405
• LogD (pH = 7.4): 1.4718733
• Log P: 1.4769042
• Molar Refractivity: 99.4227 cm^3
• Polarizability: 39.10291 Å^3
• Polar Surface Area: 103.68 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Target: Microtubule

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2254

Related research area: Cancer

REFERENCES

• Dhawan D et al. Carcinogenesis. 1999 Jun;20(6):997-1003.